Barettin
Chemical compound
From Wikipedia, the free encyclopedia
Barettin is a brominated alkaloid made of a dehydrogenated brominated derivative of tryptophan linked by two peptide bonds to an arginine residue, forming a 2,5-diketopiperazine nucleus.[1][2] It is a cyclic dipeptide and a cyclized tryptamine. The compound occurs naturally in certain sea sponges[3] and is known to interact with certain serotonin receptors.[4]
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| C17H19BrN6O2 | |
| Molar mass | 419.283 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Natural occurrence
Barettin is the major compound in the deep-sea sponge Geodia barretti.[3] It was isolated for the first time in 1986 by Göran Lidgren, Lars Bohlin and Jan Bergman at Uppsala University, Sweden[1] but the correct chemical structure was determined later in 2002.[2] Barettin is written with one 'r' because the authors misspelled Geodia barretti with one 'r' in the original paper.[1]
Pharmacology
Barettin shows affinity for the serotonin 5-HT2 receptors.[4] It has analgesic effects that are reversed by the serotonin 5-HT2A receptor ketanserin, suggesting that barettin's analgesic effects may be mediated by serotonin 5-HT2A receptor activation.[4]
Barettin seems to show antioxidant and anti-inflammatory properties which could be userful in treating diseases that affect the immune system and diseases that are caused by inflammation.[5] Atherosclerosis, a disease characterized by stiffening and a buildup of compounds in arteries,[6] may be prevented by barettin due to its anti-inflammatory properties.[5] The effects barettin has on inflammation may be due to its inhibitory properties on two protein kinases, receptor-interacting serine/threonine kinase 2 (RIPK2) and calcium/calmodulin-dependent protein kinase 1α (CAMK1α).[7]